There's a few different ways to gauge a candidate's autonomy in a sales interview. 1. Behavioral Questions: Ask situational questions that require candidates to describe times where they had to work independently to achieve sales targets or overcome challenges. For example one of my go to questions is, "What's the most creative, out of the ordinary, or above and beyond thing you’ve done to win a customer?" 2. Past Experience: Review the candidate's resume and ask about specific examples where they demonstrated autonomy in previous sales roles. Inquire about their sales process, strategies they implemented independently, and decisions they made autonomously. 3. Problem-solving Scenarios: Present examples of current sales scenarios and ask how the candidate would approach them. Evaluate whether they demonstrate the ability to think critically and make decisions independently in real life situations that arise. 4. Role-play Exercises: Conduct role-playing exercises where the candidate must handle a sales scenario independently. We ask candidates to run a discovery call and give them basic information on the team. Observe how they handle the situation and objections without much assistance or input.

There are plenty of KPIs which are not relevant if not used in the right context. Ultimately, revenue is the most important KPIs in sales. You can look at plenty of activity KPIs which are less important when revenue and pipeline are in good health. If not, then activities become more important. So it depends on the context.

To be successful in sales going forward, professionals need a mix of both soft and hard skills. Here are the most important ones to focus on: Soft Skills: 1. Emotional Intelligence (EQ): • Understanding customer emotions, handling objections, and building rapport are critical to gaining trust and maintaining strong relationships. 2. Active Listening: • Listening to what the customer says—and doesn’t say—helps identify their true needs and allows sales reps to tailor solutions effectively. 3. Resilience & Grit: • Sales is full of rejection. The ability to bounce back and maintain a positive attitude in the face of adversity is key to long-term success. 4. Adaptability: • The market, customer demands, and technologies are constantly changing. Sales professionals need to be flexible and able to pivot quickly. 5. Effective Communication: • Clear, concise, and persuasive communication, both written and verbal, is essential to conveying value propositions, closing deals, and maintaining client relationships. 6. Problem-Solving: • Customers are looking for solutions to their pain points. Being able to identify problems and provide tailored solutions separates top performers from the rest. 7. Collaboration & Teamwork: • Sales is increasingly collaborative, requiring coordination with marketing, product teams, and customer success. Building strong internal relationships helps sales professionals deliver better results. Hard Skills: 1. CRM Mastery: • Knowing how to efficiently use Customer Relationship Management (CRM) tools like Freshworks CRM for tracking leads, managing pipelines, and analyzing sales data is critical for sales effectiveness. 2. Data-Driven Decision Making: • Sales teams now rely heavily on data to inform their strategies. Sales professionals must be comfortable interpreting analytics and using data to drive decisions and forecast accurately. 3. Sales Automation & Technology Tools: • Familiarity with sales automation tools, email marketing platforms, and lead-generation software helps streamline workflows and increase efficiency. 4. Product Knowledge: • Deep understanding of the product or service you’re selling is essential. This enables you to articulate its value, answer technical questions, and position it against competitors. 5. Negotiation Skills: • The ability to navigate complex negotiations and find win-win solutions is a crucial skill for closing larger, more complicated deals. 6. Social Selling & Digital Presence: • The ability to use platforms like LinkedIn and other social networks to engage prospects, build personal brands, and generate leads is becoming increasingly important in modern sales. 7. Market & Industry Knowledge: • Understanding the broader industry landscape, competitors, and trends helps sales reps anticipate changes and position their products more effectively. Conclusion: • Soft skills such as emotional intelligence, communication, and resilience will help sales professionals build relationships and navigate challenges. • Hard skills like CRM proficiency, data analysis, and product knowledge ensure they can operate effectively and strategically. Balancing and developing these skills will help sales professionals succeed in an evolving sales environment.

This is such a great question! Having been a sales professional since 2013, I completely understand how burnout can arise, especially with the constant "reset" every quarter. What’s helped me is creating clear personal boundaries with work and sticking to a structured, repeatable process. By focusing on the things I can control and holding myself accountable to weekly, monthly, and quarterly KPIs, I’ve built a more predictable and manageable workflow. I view sales as running my own business—it requires exceptional time management and operational efficiency.

Leverage Simon Sinek's "Golden Circle" to understand the WHY, then align your enablement to the HOW and the WHAT. To ensure your efforts are aligned to the overall goals and objectives, start with some informational interviews with sales leaders gain more insight on they WHY behind the goals. Why = Understand the sales organization’s strategic objectives. Have a clear understanding as to why we are working toward these goals. How = Collaborate with sales leadership to define clear goals for enablement. What are the actions sellers will need to take to accomplish these goals. This can include the specific steps in a process, sales tools or product information, etc. as well as skills needed to successfully reach the goal. What = Ensure your enablement initiatives build the skills and simplify the processes in the HOW that will directly contribute to the company's WHY. Keep in mind that sellers do best when understanding the reasoning behind the goal and will lean into the enablement if you're aligning the HOW and WHAT to the WHY.

There is a give and take with standardizing KPIs but also having enough variance to account for things segment, (Strat, Ent, MM, Growth) number of accounts, and so on. The easiest way to have consistency and also provide a lens to inspect forecast is by implementing standardization when possible. No matter what segment you're in or how many accounts you have, if a deal is 345 days old... that's going to tell me something about the forecast accuracy of the stage it's in. I am a big fan of ensuring reps are training that in the mid point of the quarter or month, whatever your quota and cadence is, deals with a close date in quarter or in month must be in Best Case, Commit, or Closed. Nothing can be in "Pipeline" or "Omitted"

With most of these questions, there isn't a one size fits all. Consider things like: * Company stage * Growth objectives * GTM strategy * Customer segmentation * Self serve vs. sales led * Compensation modeling AI has, of course, been a hot topic lately, begging the question of which roles will become obsolete. Personally, I think there will always need to be a human element. This AMA is a great example. If you wanted these answers you could find a generic response in Chat GPT vs. reading my response, but you are looking for the human experience aspect that ideally will provide you with more value. Below is a brief rundown of how I'd think through my org structure coming in at an earlier stage business. It's less about the actual title of the role and more about the function itself: * Inbound vs. outbound * Marketing * SDR * Partner/Channel * Customer acquisition * AEs * Customer retention * Onboarding Specialists * Customer Success/Account Management * Customer expansion * AE * Customer Success/Account Management * Customer reporting * Revenue Operations * Customer value * Sales Engineers * Solution Consultants * Leadership * Revenue * Sales * Customer Success * Revenue Operations Are all of these roles needed to get started? No. Figure out where you can create overlap in your roles by working backward on your bottoms up modeling for your revenue targets and determine how many people to need in order to achieve those goals. From here, you can uplevel the structuring into categories: * Functional: Think specialists vs. generalists. Core vs. overlay * Geographic: Location specific * Market Based: Industry/vertical specific * Product Sales: For larger organizations, this can be based on product SKU, bundle, etc. to drive certain revenue engines of the business

The best sales leaders have a few things in common: -They have a deep mastery of how to sell effectively -They are incredible coaches and development focused with their team -They care a LOT about their people Why these three things? First, I've often heard the refrain that "you don't want to hire the number 1 sales rep to be a manager." That said, no one wants to follow a sales leader who isn't incredible at sales. Imagine if you had a new manager promoted over you, and their average attainment was 60% of goal. How would you feel about working for them? Not great right? So if you are interested in sales management, I would first learn how to crush your quota and become a top 15% rep. Second, the best managers I've worked with are exceptional coaches. Many new managers struggle with what we call "super-repping," where they have 7 or 8 reps, and they get on every single call and sell for their reps. Sounds great right? You tee up the call and know your manager will knock it down. But this has a hidden cost. A manager can't be everywhere at once, and their team never truly learns how to do it on their own. Coaching and development focused managers spend their time building up the skills of their reps - not to sell exactly like them - but to lean into their own style and develop 1 skill at a time, constantly adjusting the coaching to challenge the rep to push their skills further. As a manager, you have leverage (the ability to dramatically scale your impact beyond yourself) in developing great new sales people, not selling yourself. You don't want to be the hero, you want to build heroes. Third, the best managers I've ever worked with truly care about their team's success over their own. People can tell if you care. You will often make more money as a top rep, so don't become a manager unless you truly want to help build the next top performing sales rep. I once received the advice from a leadership coach that "people will forgive a lot of mistakes if you show you truly care about them" and I find that to be true. They'll also be way more committed, open to your coaching, and willing to invest their emotional energy in winning if you have their back.

Over-indexing on trying to look good by manipulating the narrative or masking challenges or flaws. Better to be honest and proactive where there are challenges, especially if it is you that has not done well enough to deliver against what is needed. Radical candor is/was talked about a lot but no matter how much practice you get the reality is it is hardest to deliver the truth when it is often most important to do so. My very first forecast call with a new CRO I was nearly certain would cost me my job. Instead, I think in part because of my honesty and directness (the news I was delivering was not good!) it turned into a pretty pivotal moment for me and my team as a result.

Great question - I find incorporating customer feedback and the insights you learn from discovery discussions into your sales process is key to driving future engagement and increasing your deal win rates. Here’s how I approach it: 1. Structured Documentation – Ensure your sellers are capturing customer/prospect insights in a standardized way (e.g., using Gong, Salesforce, or methodology templates) to track customer/prospect pain points, priorities, and desired outcomes. 2. Tailor Your Value Propositions – Then you can use these discovery insights to refine messaging, aligning your solutions directly with the customer’s needs and challenges. This makes sales conversations more relevant and compelling to hte people you are connecting with. 3. Leverage Competitive & Industry Insights – I find it key to review feedback across accounts and opportunities to identify trends, customer objections, and gaps in your positioning. It is vital that these insights get fed back to your product, product marketing and sales teams for future adjustments. 4. Training & Enablement – Enablement is key to the success of any sales process - from new hires to continuous learning. To help engrain this into your organization, equip sellers with playbooks and frameworks that incorporate real customer insights, enabling your sales team to adapt selling strategies based on real life experiences rather than relying on generic pitches. 5. Feedback to Product & Marketing – As mentioned above, work to ensure these customer insights flow back into the organization, influencing roadmap decisions, content strategy, and your competitive positioning.